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Asymmetric Iodolactonization Utilizing Chiral Squaramides.
MedLine Citation:
PMID:  23148494     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Asymmetric iodolactonization of γ- and δ-unsaturated carboxylic acids has been explored in the presence of six different chiral organocatalysts 5-8. The catalyst 6b was found to facilitate the cyclization of 5-arylhex-5-enoic acids 1 to the corresponding iodolactones 2 with up to 96% ee. By this protocol, unsaturated carboxylic acids are converted enantioselectively to synthetically useful δ-lactones in high yields using commercially available NIS. Apparently, both hydrogen bonding and aryl/aryl interactions are important for efficient stereodifferentiation.
Authors:
Jørn E Tungen; Jens M J Nolsøe; Trond V Hansen
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-13
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-14     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
School of Pharmacy, Department of Pharmaceutical Chemistry, University of Oslo , P.O. Box 1068 Blindern, N-0316 Oslo, Norway.
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